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Cheap flights from Boston (BOS) to Chicago (CHI)

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1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)

How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
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Cheap flights from Boston to Chicago in May , June 2026

27 May - 09 Jun $ 205.00
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
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24 May - 09 Jun $ 211.00
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
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18 May - 09 Jun $ 335.00
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
Pick dates

Last minute flights from Boston to Chicago

27 May - 31 May $ 257.00
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
Pick dates
24 May - 31 May $ 265.00
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
Pick dates
26 May - 31 May $ 307.00
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
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One-way flights to Chicago from Boston

7:19 AM - 7:19 AM
United Airlines
0 Stops
2h 58m
BOS - CHI
$ 99
Kiwi
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3:08 PM - 3:08 PM
United Airlines
0 Stops
2h 52m
BOS - CHI
$ 103
Kiwi
Pick dates
10:55 AM - 10:55 AM
United Airlines
0 Stops
2h 53m
BOS - CHI
$ 103
Kiwi
Pick dates

How to find the cheapest flight from Boston (BOS) to Chicago (CHI)

Related info for your journey
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.